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Holiday Vacation with Pools in Kailua, HI

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    1 / 12
    4.5 of 5 bubbles (11) Very good
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    1 / 30
    4.5 of 5 bubbles (3) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    1 / 19
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 19
    4.5 of 5 bubbles (25) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Shared Outdoor Pool...
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    About this property
    Located in a lovely beachside town, the Garden Studio is a ground floor attached studio with a private entrance and patio. The Studio is designed for relaxing and comes with a queen bed, dining table & chairs, ceiling fan, TV, air-conditioning and WiFi. Enjoy indoor or outdoor dining on the lanai.... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed 5 February 2017
    I had a wonderful time staying in this little studio! It's clean and quiet, and I had nightly gecko visitors (which I loved)! The owners are on site, and seemed like very nice...
    5 of 5 bubbles Reviewed 6 May 2016
    I don't think there is a single negative thing about this place. The late arrival was no problem and the "Surf Suite" had literally everything there- beach equipment, a grill...
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    1 / 30
    Studio, 3 Bathrooms, Sleeps 14 | Quick View
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    • Grill
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    About this property
    MINIMUM REQUIREMENTS APPLY. INQUIRE FOR DETAILS. One-of-a-kind beachside home on an exclusive street in Kailua. Perfect for a large family with kids or two families to share. Single level architect-designed home was completely rebuilt and renovated in 2007 with the highest quality tropical... View all property information
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    Kailua, Oahu 96734
    1 / 12
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Charming, very clean one bedroom house is located 300 steps from Kalama Beach Park. One of the most beautiful beaches of Hawaii. Located off the street in a very quiet residential area. It is 600 sq. ft. and has a full kitchen, all linens, A/C, beach chairs, mats, coolers, bicycles etc. There is... View all property information
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    Kailua, Oahu 96734
    1 / 25
    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
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    • x
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    About this property
    Peaceful Energy of Maluhia Let the relaxing atmosphere of Maluhia whisk you into vacation-mode! The tropical pool will make you feel like you are swimming in the middle of your own private lagoon while a heated Jacuzzi will relax your body at the end of the day. The covered barbecue lanai area has... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 41
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Private Garden
    • Patio
    • Grill
    • Private Outdoor...
    • Satellite TV
    • Parking
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This island style, open floor plan, family home is a five minute walk to Kailua beach. The huge lawn, play house, fire pit and saltwater pool (child safety fence upon request for a nominal set up charge) make this a fabulous home for families with kids. The adults will appreciate the gourmet, all... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed 14 February 2017
    From the moment we pulled into the private gated driveway of this beautiful island home, we new we were in for a vacation we would never forget! The home is impeccably...
    5 of 5 bubbles Reviewed 10 February 2017
    We can't say enough good things about our recent stay at Holona Hale in Kailua! Our three sons are 9, 7 and 4, and if it was up to them we would have never left the property!! The...
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    1 / 37
    4 of 5 bubbles (1) Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    • Grill
    • Satellite TV
    • Internet Access
    • DVD Player
    • Private Outdoor...
    • Washer
    • Hot Tub
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    • Pet-friendly
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    • x
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    • x
    About this property
    Privacy and comfort are provided in this luxury Hawaiian/Asian furnished home. This 4000 sq ft. gated property with an 8 ft wall surrounding the perimeter is on a double lot in the heart of Kailua, less than one mile from Kailua/Lanikai beaches and Kailua town. The home and additional villa unit... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 28
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • Parking
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    • Balcony
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    • x
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    About this property
    ***Longer minimum stay requirements may apply.  Rates may vary depending on length of stay.  Inquire for possible DISCOUNTS*** Lanikai Beach Cottage The charming beach cottage has two separate dwellings on property that are rented together to provide 3 bedrooms and 2 baths. The main house is 2... View all property information
    Location Information
    Kailua, Oahu 96734
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    1 / 15
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 13 | Quick View
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    • Private Outdoor...
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    • Grill
    • Satellite TV
    • Porch
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    • x
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    • x
    About this property
    A very nice updated 5 bedroom home that is located on a side street with no traffic. The beach entrance is a private street entrance 2 blocks away so you can walk to the beach but not have a large crowd of people on the beach. It is a very safe all white sand beach that is great for family's and... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 32
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • DVD Player
    • Washer
    • Internet Access
    • Grill
    • Private Outdoor...
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    • Pet-friendly
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    • x
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    About this property
    Description The Ohana Beachfront Villa is a 5-bedroom, 5.5 bathroom estate that offers a great view of Kailua Beach. You can enjoy the view from the ocean lanai and garden lanai, along with the landscaping. One of the best features of this home is a lagoon-style pavilion with tropical waterfalls... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Mountain Views
    • Private Outdoor...
    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Satellite TV
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Kaimalino Kai is a two story, 3 bedroom, 3 bathroom oceanfront gem perched elegantly against the backdrop of Kailua Bay. Hear the sound of the waves crashing against the rocky shoreline while magical ocean views complement elegant indoor and lush outdoor spaces. Live each moment of your relaxing... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 73
    5 of 5 bubbles (4) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Ocean Views
    • Internet Access
    • Waterfront
    • DVD Player
    • Washer
    • Mountain Views
    • Children's Pool
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our home is located DIRECTLY on the Beach. Arguable the BEST BEACH, the BEST VIEWS, and on the BEST BEACH ACCESS in Hawaii. WONDERFULLY soft and manicured yard. LOTS of TEAK: lounge chairs, rocking chairs, porch swing, picnic tables, and accessories -THE HOUSE: Our home is tastefully decorated... View all property information
    Location Information
    Kailua, Oahu 96734 2324
    5 of 5 bubbles Reviewed 31 May 2015
    Our family got to spend a week in paradise in Dan's home. The view from the lanai is outstanding. Steps to the beach, all the beach and water toys one could ever hope for, perfect...
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    1 / 21
    4 of 5 bubbles (1) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
    • DVD Player
    • Hot Tub
    • Grill
    • Private Outdoor...
    • Washer
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Description Breath-taking views... luxurious details... this is Shangri-La by the sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Rejuvenate your mind, and cherish friends and family as you settle into this... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 19
    4.5 of 5 bubbles (3) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
    • Shared Outdoor Pool...
    • DVD Player
    • Grill
    • Mountain Views
    • Patio
    • Washer
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • ?
    About this property
    Aloha from the island of Oahu, and welcome to paradise! Ko'olau Vista Villa is a large, private, two-story family home with, four-bedrooms plus bonus room ( 5th bedroom), four-bath property located in beautiful Kailua, Hawaii. Known for its small town charm and friendliness, Kailua also offers... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 bubbles Reviewed 10 January 2014
    Lots & lots of room. Family of 7 - 2 kids (8&10), 2 couples & single. So there was plenty of space that we could stay out of each others hair and off each others nerves. We...
    5 of 5 bubbles Reviewed 19 December 2013
    Our family of four, my friends family of 5 and my Mom and step father stayed here for 10days. I would recommend it. the beds were comfortable, as was the house. There was no air...
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    1 / 44
    Studio, 8 Bathrooms, Sleeps 15 | Quick View
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    • Parking
    • Waterfront
    • DVD Player
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    • Hot Tub
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    The Essence of Kailua Beach Living Castle Point Estate is an estate built to embody the essence of luxury Kailua Beach living. Bringing in the elements of the ocean, bold colors bounce off soft hues and simplicity offers a space where natural beauty can be enjoyed. Built with intention, it's new... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Parking
    • Private Outdoor...
    • Patio
    • Air Conditioning
    • Grill
    • Washer
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Come experience the beauty of Kailua. Stay in our charming 'Hale Nalu Palekaiko ' Surf Paradise Home. See why people call Kailua 'Papalani' Heaven on earth! Relax in our charming and comfortable 3 bedroom, 2 bathroom hale. We also have a ohana/cottage that can be rented with the main hale. The... View all property information
    Location Information
    Kailua, Oahu
    1 / 35
    Studio, 6 Bathrooms, Sleeps 8 | Quick View
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    • Mountain Views
    • Satellite TV
    • Internet Access
    • Private Outdoor...
    • Hot Tub
    • Waterfront
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    Luxury awaits! As Kailua's tallest oceanfront home, Whispering Palms offers unparalleled 280 degree views. Watch the sunrise or moon rise over the Mokulua Islands or the turtles and fish swimming outside your window. Beyond it's magnificent double art glass doors, you'll fine the Hawaiian home of... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 38
    Studio, 7 Bathrooms, Sleeps 14 | Quick View
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    • Shared Outdoor Pool...
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    • x
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    • Smoking allowed
    • x
    About this property
    Built by famous stylist Paul Mitchell in the late 1980s. This gated, beachfront, landmark property was designed with natural spaces and architecture that reflect the social and welcoming Polynesian lifestyle - a home that's not only beautiful, but also strikes the perfect balance between privacy,... View all property information
    Location Information
    Kailua, Oahu 96734
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    1 / 20
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Private Outdoor...
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    • Waterfront
    • Mountain Views
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    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Breath-taking views . . . luxurious details . . . This is Shangri-La by the Sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Rejuvenate your mind, and cherish friends and family as you settle into this luxurious,... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 30
    4.5 of 5 bubbles (8) Very good
    3 Bedrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
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    • Mountain Views
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    • Patio
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    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Aloha and welcome to your beach house. This charming home has everything you need for your dream vacation. Bring your family and friends to unwind Island-style. Come on in and make yourself comfortable. As soon as you walk through the door the stress of everyday life will melt away. Most of the... View all property information
    Location Information
    Kailua, Oahu 96734
    5 of 5 bubbles Reviewed 19 August 2015
    Our stay was enhanced by the fact that the owners were available if and when there was any problem. I wondered what I would do if there were an emergency, car problems or medical...
    5 of 5 bubbles Reviewed 11 August 2015
    We have dreamed of going to Hawaii all of our lives and finally had the opportunity to go for our dream trip. I have to say that all of our expectations of Hawaii were filled...
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    1 / 6
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • DVD Player
    • Waterfront
    • Internet Access
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    • Mountain Views
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Old Hawaiiana steps from the world-famous, Lanikai Beach, this three bedroom, three bath retreat has the true feel of the Hawaii of yester-year. Hale Maluhia is tropically decorated with all amenities for your comfort. Art work has been hand selected from local artists. Marble and Travertine... View all property information
    Location Information
    Kailua, Oahu 96734
    4 of 5 bubbles Reviewed 13 August 2015
    The pictures of this home on TripAdvisor do not do it justice. This is a high-quality 3BR, 3BA home. Each BR has its own en suite. Perhaps not suitable for very young kids...
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    1 / 28
    Studio, 6 Bathrooms, Sleeps 14 | Quick View
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    • Air Conditioning
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    • x
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    • x
    About this property
    With access to the world-famous Kailua Beach and its turquoise waters being just four houses away and shops, restaurants and grocery nearby, the location of Helen's Beach House could not be more ideal. The exterior maintains a modest aesthetic, but this only serves as a cover of sorts for how... View all property information
    Location Information
    Kailua, Oahu 96743
    1 / 41
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Satellite TV
    • Patio
    • Waterfront
    • DVD Player
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Kailua oceanfront deluxe vacation rentals - two units located in oceanfront home in Kailua on the ocean. One unit faces the mountains and the outer faces the ocean. Both have separate entrances, bathrooms, and kitchenette facilities. These are deluxe rooms with 16-foot vaulted ceilings, air... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 39
    4.5 of 5 bubbles (5) Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Satellite TV
    • Washer
    • Air Conditioning
    • Internet Access
    • Sauna
    • Private Outdoor...
    • Waterfront
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Step back in time and experience a peaceful, private Hawaiian lifestyle at this one of a kind beach house located on a million dollar beach front lot. This home has over 3,100 spacious square feet of living space. The 6 bedrooms surround the large courtyard with a private pool, creating a very... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 19
    5 of 5 bubbles (6) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    5 Minute Walk To Beach * Ocean View Beachside Home * Wrap-around Lanai * Spacious 2,200 SF 3BR, 2.5BA Home * Pool * Full Service Gourmet Kitchen * BBQ * Huge Master * Indoor Laundry * TV & WIFI * Parking * 2 Mile Walking Loop * Golf * Hiking Trail * Playground * Park * Also Available 600 SF 1BR -... View all property information
    Location Information
    Kailua, Oahu 96734
    1 / 40
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Ohana Beach House is an elegant beach home ideally located just steps from world famous Lanikai Beach. It’s light blue, sea foam green and white-washed wood décor give it a beachy island style, while warm colors, oversized rooms and fine linens give it a cozy and comfortable feel. The home itself,... View all property information
    Location Information
    Kailua, Oahu 96734